$727,852Average Value$378Average Price per Sq Ft51Homes For Sale
Serene residential area in Guilford with various homes nestled among lush greenery.
A place with something for everyone
Guilford is a coastal Connecticut town that, at first glance, resembles a small town reminiscent of a 1960s-era television show. With its quaint and historic downtown sector lined with quaint local retailers, the 12-acre Guilford Town Green that is the site of various performances throughout the year and the quiet, tree-lined streets, Guilford provides an almost country feeling, like something out of a brochure for a New England bed-and-breakfast. But look a little closer and it’s also a vibrant, cosmopolitan town with a bevy of amenities, superb schools and beautiful homes, not to mention the fact that Guilford abuts Long Island Sound on its southern border, affording residents easy access to the beach and the ocean beyond. “People come here because they want waterfront and seclusion,” says local Realtor Karen Stephens of Compass, who has been representing transactions in the area for more than 20 years. “And the properties are quite amazing.” It’s that combination of qualities that leads Guilford First Selectman Matthew Hoey to describe Guilford as “a place with something for everyone.”
Out and about in Guilford
Because of its proximity to Long Island Sound, Guilford is a haven for lovers of the sea. Mariners can keep their vessels at the Guilford Marina, and members of the Guilford Yacht Club can access both slips and moorings, as well as the club’s tennis, dining and other social facilities. Jacob’s Beach is a 25-acre coastline retreat on the Sound, where kids can play on the playground and visitors of all ages can enjoy the open, sandy beach and grassy space perfect for sunbathing or a picnic. Further inland is Lake Quonnipaug, a prime spot for catching a variety of freshwater species, and also a perfect spot for swimming or relaxing on the lakeside beach. Hikers head to Timberland Preserve, a 600-acre expanse with more than 15 miles of trails, and golfers can tee off at the nine-hole Guilford Lakes Golf Course.
The centrally located Guilford Town Green is a favorite community gathering spot, serving as the site of a summer concert series, the town’s annual Halloween and holiday tree-lighting festivals, the GreenStage Guilford Live music festival and a variety of other programs throughout the year. “People come from all around for these events,” says Stephens. And don’t be too surprised if exotic animals suddenly appear on the Green, as a local anonymous artist periodically places two-dimensional (although quite lifelike) replicas of polar bears, penguins and other Arctic-dwelling animals on the Green to celebrate the season’s first snowfall. After residents have had a chance to see the art installation, the animals are auctioned off to benefit Meals and Wheels.
Serene beachside park located at Jacob's Beach in Guilford overlooking a tranquil sandy beach.
Bittner Park in Guilford features calm areas to host picnics with the family.
Serene landscape of Guilford showcasing a tranquil marsh with golden tall grass.
1/3
Top-rated schools
The Guilford Public Schools district earns an overall grade of A from Niche, and the area’s exceptional schools include A. W. Cox Elementary, Adams Middle and Guilford High School, all of which earn an A from Niche. Students at Guilford High School have the opportunity to participate with more than 35 school-sponsored clubs, can audition for the school’s award-winning theater program and have the opportunity to play more than 15 varsity-level sports. There are also several renowned private schools in the area, including nearby Choate Rosemary Hall, ranked as the best private school in the state by Niche, which gives it an A-plus rating.
Guilford Lakes School is conveniently located on Maupas Road.
Students are proud to call Guilford High School their place for learning.
1/2
From 18th century colonials to modern homes
Guilford has the distinction of being home to one of the largest collections of historic homes in New England, including the 1693 Henry Whitfield House, that today serves as a museum. The Whitfield House is the oldest house in Connecticut and the oldest stone dwelling built by North American settlers. And while buyers will find homes here for sale that were built as far back as the 18th century, there are plenty of options for those who prefer new construction, too. The median price in the area is $590,000, and buyers should expect to pay an average of $341 per square foot. A two-bedroom/two-bathroom ranch-style home in need of some TLC can sell for as low as $200,000, and prices can go up to nearly $6 million for a four-bedroom/three-bathroom colonial on a private waterfront peninsula with a private beach.
Picturesque Colonial style home in Guilford with a vibrant blue door and a cozy porch.
Two story home in Guilford with a neat driveway and a calm street in the foreground.
Modern home in Guilford with a manicured lawn and a calm ambiance in the background.
1/3
Plentiful options for shopping and dining
With Big Y located in the center of town, residents don’t have to drive far for grocery shopping trips, and Bishop’s Orchards offers the opportunity for visitors to pick their own fruit in-season, typically from June through October. Walmart is located next to Big Y for any home necessities. Downtown Guilford has an array of local boutiques and shopping opportunities, and the Connecticut Post Mall – the largest mall in the state – is located in Milford, just over 20 miles away.
When dining out, Guilford Mooring is a popular destination for fresh seafood served in a waterfront setting. For a little more upscale occasion, Chapter One is well-known for exceptional service and a wide-ranging menu featuring burgers, steaks and seafood, as well as vegetarian and vegan options. And for a little grab-and-go, Cinco de Mayo Food Truck located at the north end of Guilford Town Green prepares well-known Mexican favorites for a relaxing lunch in the park.
Residents of Guilford enjoy strolling on vibrant streets featuring quaint local businesses.
Lobster Pound in Guilford is known for their incredible Hot Lobster Roll.
Charming town of Guilford as pedestrians stroll past boutique storefronts.
1/3
Getting out of town
Commuters here have easy access to Interstate 95, which bisects the middle of Guilford, make the 16-mile trip to New Haven. Alternatively, the CTrail Shore Line East train leaves from the Guilford Station, with service to New Haven taking about 20 minutes, where riders can connect to trains going south to New York City or north to Boston.
Guilford Train Station offers residents direct access to neighboring towns and cities.
Guilford Train Station provides easy commuting for residents into New Haven.
1/2
Photography Contributed By
Fabio Riso
Video By
Matthew Bloch
Interested in learning more about homes in this area?
Reach out to
Nick Prevost,
an experienced agent in this area.
On average, homes in Guilford, CT sell after 62 days on the market compared to the national average of 52 days. The median sale price for homes in Guilford, CT over the last 12 months is $625,000, up 7% from the median home sale price over the previous 12 months.
Don't miss your opportunity to see this lovely 4-Bedroom 2.5 bath colonial located at the end of a quiet cul-de-sac featuring many recent updates. This beautifully maintained home offers ample space, outdoor privacy, unique character and charm. So much curbside appeal with impressive stone walkways, stone walls, and vibrant perennial gardens. Step inside to discover a warm and inviting interior
Coastal Comfort & Classic Charm in Guilford's Sunrise District. Welcome to 42 Horseshoe Road, a beautifully updated three-bedroom, 1.5-bath home. Set on a level, sun-filled lot, this property offers the perfect blend of tranquility and convenience just moments from the shoreline and town amenities. Step inside to discover newly finished Hardwood floors that glow with warmth and character. While
Discover this bright and inviting 3-bedroom, 2.5-bath raised ranch tucked away on a quiet cul-de-sac in desirable Guilford. Set on just over an acre and framed by mature trees, the property offers a private, tranquil setting while remaining close to town and schools. Inside, hardwood floors flow through the main living areas, enhancing the open, airy feel. A sunroom provides year-round natural
Introducing a custom-built Adirondack-style masterpiece, set on over 5 acres of pristine land. Designed with care by the current owners, this home boasts a seamless layout, ideal for entertaining. Spacious, elegantly appointed rooms feature a custom-designed kitchen, soaring ceilings, and a stunning two-sided stone fireplace. Each bedroom is en suite, offering both privacy and luxury. The
Welcome to a charming ranch style home perfectly tucked away on a quaint cul-de-sac, located in the Guilford Lakes Associat Step into the inviting family room, featuring a vaulted ceiling, skylights and a slider that opens to a lovely patio-ideal for soaking in the serene surroundings. The living room boasts built-in bookcases, perfect for showcasing your favorite reads. The large screened porch
Welcome to 360 Jefferson Drive! This charming four-bedroom, 2.5 bath colonial is set back from the road on a beautiful level lot with a wooded border, offering both privacy and curb appeal. Inside, you'll find a spacious layout featuring a comfortable family room with a fireplace, a formal living room, and a dining room perfect for entertaining. The kitchen includes a relaxed eating area,
HOUSE COMES FULLY FURNISHED, RENT BY OWNER, AVAILABLE AUGUST 30, 2025, ACADEMIC RENTAL HOME HAS A NICE COZY FEEL TO IT, WITH FIREPLACE IN THE FAMILY ROOM, FULLY EQUIPPED KITCHEN, STAINLESS STEEL APPLIANCES. VERY EFFICIENT HOME FRESHLY PAINTED WITH NEW WELL WATER TREATMENT, FURNACE AND CENTRAL AIR CONDITIONING SYSTEMS. DOWNSTAIRS HOME OFFICE, LARGE FAMILY/PLAYROOM, HALF BATHROOM AND LAUNDRY AREA.
Welcome to your new home at 20 River Colony, Guilford, CT! New quartz countertops, stainless steel appliances and entire unti is freshly painted and bedroom windows are being replaced with Anderson windows. This charming first-floor ranch offers 2 bedrooms and 1 bathroom across 894 square feet has two sliders to patio with lots of light. Relax on your private patio with lovely views of the open
Riverside Retreat in the Heart of Guilford Escape to your own private sanctuary in this thoughtfully updated top-floor end unit, where the gentle sounds of the nearby river create the perfect soundtrack for daily life. Tucked away in a well-maintained boutique community, this serene haven offers the best of both worlds-peaceful riverside living with downtown Guilford just steps from your door.
Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
